Skip to main content
Lenny's Podcast

How to find hidden growth opportunities in your product | Albert Cheng (Duolingo, Grammarly, Chess.com)

85 min episode · 2 min read
·
Albert Cheng

Episode

85 min

Read time

2 min

Topics

Remote Work, Startups, Fundraising & VC

AI-Generated Summary

Key Takeaways

  • Explore and Exploit Framework: Find winning experiments then systematically expand learnings across the product. When Chess.com discovered users prefer reviewing wins over losses, they made game review 25% more positive, growing reviews by 25% and subscriptions by 20%, then applied positivity patterns to adjacent features like puzzles and challenges.
  • Freemium Sampling Strategy: Grammarly doubled upgrade rates by interspersing paid suggestions among free ones instead of only showing spelling and grammar corrections. This counterintuitive approach gave free users a taste of premium features without cannibalizing paid conversions, demonstrating the product's full value proposition beyond basic correctness.
  • Experimentation Volume Targets: Chess.com went from zero experiments to targeting 1000 annually by enabling no-code testing, expanding experiments beyond product to lifecycle marketing, App Store optimization, and content. The goal itself matters less than conversations about what infrastructure and cultural changes enable that velocity.
  • Current User Retention Priority: For daily-use products, existing user retention compounds far more than new user acquisition. Duolingo found 80% of daily active users are current or resurrected users, not new signups. Day one retention of 30-40% indicates product-market fit for consumer apps with sufficient frequency and scale.
  • AI-Powered Analysis Tools: Text-to-SQL Slack bots answer ad-hoc data questions instantly without analyst bottlenecks, dramatically increasing company-wide data literacy. This removes embarrassment barriers that prevent people from asking questions, creating an explosion of inquiry that surfaces hidden insights and accelerates learning cycles across growth teams.

What It Covers

Albert Cheng, growth leader at Duolingo, Grammarly, and Chess.com, shares his explore-and-exploit framework for finding growth opportunities, biggest monetization wins including Grammarly's freemium sampling strategy that doubled upgrade rates, and experimentation best practices.

Key Questions Answered

  • Explore and Exploit Framework: Find winning experiments then systematically expand learnings across the product. When Chess.com discovered users prefer reviewing wins over losses, they made game review 25% more positive, growing reviews by 25% and subscriptions by 20%, then applied positivity patterns to adjacent features like puzzles and challenges.
  • Freemium Sampling Strategy: Grammarly doubled upgrade rates by interspersing paid suggestions among free ones instead of only showing spelling and grammar corrections. This counterintuitive approach gave free users a taste of premium features without cannibalizing paid conversions, demonstrating the product's full value proposition beyond basic correctness.
  • Experimentation Volume Targets: Chess.com went from zero experiments to targeting 1000 annually by enabling no-code testing, expanding experiments beyond product to lifecycle marketing, App Store optimization, and content. The goal itself matters less than conversations about what infrastructure and cultural changes enable that velocity.
  • Current User Retention Priority: For daily-use products, existing user retention compounds far more than new user acquisition. Duolingo found 80% of daily active users are current or resurrected users, not new signups. Day one retention of 30-40% indicates product-market fit for consumer apps with sufficient frequency and scale.
  • AI-Powered Analysis Tools: Text-to-SQL Slack bots answer ad-hoc data questions instantly without analyst bottlenecks, dramatically increasing company-wide data literacy. This removes embarrassment barriers that prevent people from asking questions, creating an explosion of inquiry that surfaces hidden insights and accelerates learning cycles across growth teams.

Notable Moment

Chess.com discovered through tracking that 80% of users review games after wins, not losses as expected. Flipping the post-loss experience to show brilliant moves instead of blunders with encouraging coach messages grew engagement dramatically by aligning with human psychology over logical assumptions.

Know someone who'd find this useful?

Episode Transcript

Growth is the job is to connect users to the value of your product. Growth sometimes gets this reputation that it's just pure metrics hacking. You worked at three of the most successful consumer subscription products in the world. Where do you think is the biggest missing piece that people don't get about building a successful consumer subscription product? User retention is gold for consumer subscription companies. If you don't retain your users, then a lot of the onus is on getting them to pay on day one. Noam Levinsky, he said that I need to ask you about the biggest monetization win that you found at Grammarly. The lived product experience for most of the free users was that Grammarly was just a product to fix your spelling and grammar because those were the free suggestions. What if we actually sampled a number of different paid suggestions and interspersed them to free users counterintuitive lesson you've learned about building teams? I saw some of the highest performers just being people that had very high agency, had that clock speed, had that energy, but they didn't necessarily need to have deep experience on that matter. Sometimes experience could be a crutch, especially in this world where the grounds are shifting so fast with AI. A lot of your learned habits actually need to be intentionally discarded. Today, my guest is Albert Chang. Albert is known as one of the top consumer growth minds in the world. He led growth and monetization at three of the most successful and beloved consumer products in the world, Duolingo, Grammarly, and now chest.com. Earlier in his career at YouTube, he worked on streaming and gaming features used by over 20,000,000 people. His unique approach to growth blends marketing, data, strategy, and product management. And in our conversation, we cover a lot of ground, including his explore and exploit framework to find growth opportunities, his biggest and most interesting growth wins at Duolingo, Grammarly, and chess.com, how he uses AI to accelerate his growth work, what he's come to realize about the power of brand and community in your growth work, his top experimentation best practices, why his goal at every company is to run 1,000 experiments a year, and so much more. A huge thank you to Eric Albest, Noam Levinsky, and Jorge Masal for suggesting topics for this conversation. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It helps tremendously. Also, if you become an annual subscriber of my newsletter, you get 15 incredible products for free for an entire year, including Lovable, Replit, Bolt, NNN, Linear, Superhuman, Descript, Whisperflow, Gamma, Perplexity, Warp, Granola, Magic Patterns, Raycast, JP, RD, and Mobbin. Head on over to lenny'snewsletter.com and click product tasks. With that, I bring you Albert Chang. My podcast guests and I love talking about craft and taste and agency and product market fit. You know what we don't love talking about? …

Get the full transcript (17,102 words) + summary by email — free

One-time email with the complete transcript and AI summary of this episode. No account needed.

One email, no spam. We’ll also show you what SignalCast does.

Browse all Lenny's Podcast transcripts →

You just read a 3-minute summary of a 82-minute episode.

Get Lenny's Podcast summarized like this every Monday — plus up to 2 more podcasts, free.

Pick Your Podcasts — Free

Keep Reading

Books, tools, and gear mentioned in this episode

SignalCast may earn commission on purchases via these links.

company

  • Albert Cheng, growth leader at Duolingo, Grammarly, and Chess.com... Grammarly doubled upgrade rates by interspersing paid suggestions among free ones.
  • Albert Cheng, growth leader at Duolingo, Grammarly, and Chess.com... Duolingo found 80% of daily active users are current or resurrected users, not new signups.
  • Albert Cheng, growth leader at Duolingo, Grammarly, and Chess.com... When Chess.com discovered users prefer reviewing wins over losses, they made game review 25% more positive.

More from Lenny's Podcast

We summarize every new episode. Want them in your inbox?

Similar Episodes

Related episodes from other podcasts

Explore Related Topics

This podcast is featured in Best Product Management Podcasts (2026) — ranked and reviewed with AI summaries.

Read this week's Startups & Product Podcast Insights — cross-podcast analysis updated weekly.

You're clearly into Lenny's Podcast.

Every Monday, we deliver AI summaries of the latest episodes from Lenny's Podcast and 192+ other podcasts. Free for one show.

Start My Monday Digest

No credit card · Unsubscribe anytime